Top Chief Of Staff Jobs in Chicago, IL

Lead and deliver medium-to-large cross-functional projects, manage the operational rhythm of the business (meetings, OKRs, reporting), drive internal communications and engagement, identify process improvements, manage risks/issues, and partner with stakeholders to ensure on-time, on-budget delivery.

Partner with the Chief People Officer to shape People strategy, run operating rhythms, prepare executive-ready materials, manage cross-functional initiatives, and lead high-priority confidential projects to drive alignment and execution across the People organization.

Leads commercial growth initiatives from concept through traction, including market sizing, business cases, go-to-market strategy, competitive intelligence, and cross-functional execution. Drives executive committee operating rhythms, board preparation, strategic initiative tracking, decision-making, and accountability across Product, Clinical, Marketing, Finance, Sales, and executive stakeholders.

Serve as chief of staff to the SVP for U.S. and Canadian payment markets, translating strategy into execution. Lead cross-functional programs, manage and sequence multiple projects, apply quantitative and qualitative analysis to solve ambiguous problems, drive executive communications, and improve business performance across product, technology, finance, and operations.

Serve as a strategic partner to the Head of Engineering and leadership team during rapid organizational growth. Own operating rhythms, improve decision-making and execution, diagnose organizational friction, and create plans for cross-functional delivery. Translate technology strategy into priorities, operating plans, and measurable outcomes. Apply AI tools to streamline processes and reduce operational toil while influencing senior technical leaders and driving sustainable organizational practices.

Serve as strategic partner to the Enterprise GM to design and execute multi-year strategies and operating models. Lead cross-functional initiatives, align executive priorities and resource allocation, drive organizational change and operational excellence, synthesize insights for senior decision-making, and build relationships across VP+ leaders to mobilize company-level transformation.

Serve as strategic partner to the SVP of Product to scale product leadership: run leadership rhythms, own headcount and budget planning, drive AI enablement, curate external product narrative, manage org-health metrics, and resolve cross-functional structural issues to increase decision speed and org effectiveness.

Serve as Chief of Staff to the CHRO, managing the People leadership operating cadence, leading cross-functional initiatives end-to-end, crafting executive communications, resolving issues proactively, and representing CHRO priorities across the organization.

Senior strategic leader supporting fundraising, operations, and organizational initiatives for Medicine and Biological Sciences Development. Manages major gifts portfolio, teams (up to 30 staff), research/analytics, donor relations, outreach, and marketing. Drives affiliate and international fundraising, partners with senior leadership and trustees, represents the Vice President, and leads campaign execution, special projects, prospect cultivation, solicitation, and stewardship to meet ambitious philanthropic goals.

Seeking a Chief of Staff across portfolio companies: an all‑star generalist with 2–4 years' experience in high‑growth startups, banking, consulting, or other high‑intensity environments. Candidates submit details for consideration against openings.

Chief of Staff partnering directly with the CEO to improve company operations, product execution, metrics, leadership effectiveness, and AI enablement. The role owns the product operating system, cross-company dashboards, roadmap coordination, executive meeting processes, strategic product insights, and high-impact special projects. It requires a highly quantitative, product-oriented operator who can lead independently, communicate exceptionally, and drive accountability across a remote, founder-led startup.

The Chief of Staff will lead AI transformation projects, manage investment funds, drive sales initiatives, and oversee client project delivery, requiring self-direction and proactivity.

The Chief of Staff will oversee operational projects, refine strategies, and support leadership in a fast-paced scaling environment.

The BizOps Lead will advise the CEO, manage strategic initiatives, coordinate programs, prepare communications for stakeholders, and lead special projects.

Serve as the CEO's strategic and operational right hand at an AI LegalTech startup: prepare executive/board/investor materials, build financial models and decks, contribute litigation expertise to product content, validate LLM-generated analyses, drive cross-functional execution, manage company operations (recruiting, vendor administration, OKRs), represent the CEO, and handle special projects across finance, legal, and partnerships.

Serve as CEO's trusted advisor and operational leader to align the executive team, drive strategic initiatives, build operating systems and KPI frameworks, lead cross-functional execution, and improve organizational communication and decision-making to enable faster, smarter outcomes.

Support the executive by cutting administrative workload 50% within 30 days, convert tribal knowledge into SOPs, manage weekly/6-month/2-year OKRs and org chart, configure productivity tools, proactively solve problems, and ensure clear, error-free communication across teams.

Serve as a strategic operator and force multiplier for the CEO and leadership team. Drive cross-functional initiatives, prepare Board and investor materials, enable AI adoption and build workflows, support finance and revenue analytics, coordinate leadership rhythms and company offsites, and translate executive priorities into measurable plans and follow-through.

Partner with the CEO to translate strategy into executable plans, lead high-priority cross-functional initiatives, monitor business metrics, synthesize insights for decision-making, and coordinate across merchandising, marketing, e-commerce, operations, finance, and retail/wholesale partners.

The Chief of Staff to the CEO will manage the company's operating system, drive strategic projects, facilitate communication, and align leadership priorities with a strong commitment to healthcare access.

Strategic partner to the Co-CEOs driving alignment, execution, and communication across goop’s business, Gwyneth’s media/personal portfolio, and investments. Build AI-enabled Notion dashboards and automations, run executive meetings, prepare board decks and briefings, manage CRM and relationship health, lead cross-functional strategic projects, and support company-wide communications and offsite planning.

Manage the Enterprise Deployment team’s workflow, staffing, performance tracking, recruiting coordination, onboarding, meetings, OKRs, team gatherings, and cross-functional alignment. The Chief of Staff will optimize team efficiency, thoughtfully allocate people to projects, identify performance or coverage gaps, and serve as a trusted liaison to organizational leaders. This is a fully remote global role, with London preferred.

The Chief of Staff serves as a strategic partner to the CEO and COO, managing executive operating cadence, board and investor relations, enterprise initiatives, OKRs, strategic planning, and organizational effectiveness. The role leads fundraising strategy across venture, philanthropic, and government sources, including pipeline management, grant execution, investor materials, and stakeholder engagement. It also coordinates executive meetings, tracks KPIs, supports decision-making, and manages cross-functional projects. Travel to markets, conferences, and company meetings is approximately 20–25%.

Partner with the COO to lead and execute firmwide strategic initiatives, run operating cadence, prepare executive and Board materials, build operational infrastructure, and drive AI adoption and governance across the business.

Partners with the CEO and executive team to drive company strategy, business operations, revenue and sales operations, business systems, AI infrastructure programs, and special projects. Leads KPI tracking, executive cadence, cross-functional program execution, PMO operations, acquisition due diligence and integration, systems optimization, forecasting, and organizational alignment across global functions.